Synthesis of stereodefined polysubstituted olefins. 1. Sequential intermolecular reactions involving selective, stepwise insertion of Pd(0) into allylic and vinylic halide bonds. The stereoselective synthesis of disubstituted olefins

被引:71
作者
Organ, MG [1 ]
Cooper, JT [1 ]
Rogers, LR [1 ]
Soleymanzadeh, F [1 ]
Paul, T [1 ]
机构
[1] York Univ, Dept Chem, N York, ON M3J 1P3, Canada
关键词
D O I
10.1021/jo001045l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin beta -D-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.
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页码:7959 / 7970
页数:12
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